Cationic Thorium Alkyl complexes of rigid NON- and NNN-donor ligands: π-arene coordination as a persistent structural motif

Organometallics

Volumn 28, Issue 6, 2009, Pages 1891-1899

  Cruz, Carlos A ^a   Emslie, David J H ^a   Robertson, Craig M ^a   Harrington, Laura E ^a   Jenkins, Hilary A ^a   Britten, James F ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2D-NMR SPECTROSCOPIES; ALKYL COMPLEXES; CONTACT ION PAIRS; DIALKYL COMPLEXES; DINUCLEAR; DINUCLEAR CATIONS; DONOR LIGANDS; ION PAIRS; LIGAND BRIDGINGS; MONOCATION; NMR SPECTROSCOPIES; ROOM TEMPERATURES; STRUCTURAL MOTIFS; X-RAY CRYSTALLOGRAPHIES;

BENZENE; DYES; FULLERENES; HEXANE; LIGANDS; MINERALOGY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITIVE IONS; SELF ASSEMBLY; TOLUENE;

X RAY CRYSTALLOGRAPHY;

EID: 64649106502     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800624t     Document Type: Article

References (99)

1. (a) Alt, H. G.; Köppl, A. Chem. Rev. 2000, 100. 1205.
2. (b) McKnight, A. L.; Waymouth. R. M. Chem. Rev. 1998. 98, 2587.
3. Gibson, V. C; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283.
4. (a) Gromada, J.; Carpentier, J. F.; Mortreux, A. Coord. Chem. Rev. 2004. 248, 397.
5. (b) Zeimentz. P. M.; Arndt, S.; Elvidge, B. R.; Okuda, J. Chem. Rev. 2006, 106, 2404.
6. (c) Hou, Z.; Wakatsuki, Y. Coord. Chem. Rev. 2002. 231, 1.
7. Jia, L.; Yang, X.: Stem, C. L.; Marks, T. J. Organometallics 1997, 16, 842.
8. Chen, Y.-X.; Stern, C. L.; Yang, S.; Marks. T. J. J. Am. Chem. Soc. 1996, 118, 12451.
9. (a) Jia, L.; Yang, X.; Stern, C: Marks, T. J. Organometallics 1994, 13, 3755.
10. (b) Lin, Z.; Le Marechal, J.-F.; Sabat, M.; Marks, T. J. J. Am. Chem. Soc. 1987, 109, 4127.
11. Yang, X.; King. W. A.; Sabat, M.; Marks, T. J. Organometallics 1993, 12, 4254.
12. Yang, X.; Stern, C. L.; Marks. T. J. Organometallics 1991, 10, 840.
13. Chen, Y. X.; Metz, M. V.; Li, L. T.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 6287.
14. 2 has been proposed on the basis of elemental analysis: Evans, W. J.; Nyce. G. W.; Ziller, J. W. Organometallics 2001, 20. 5489.
15. See, for example: (a) Marks, T. J.; Ja, L.; Yang, X. U.S. Patent 5,477,895, 1995.
16. (b) Marks. T. J.; Chen, Y.-X. U.S. Patent 6,229,034 Bl, 2001.
17. (c) Marks, T. J.; Chen, Y.-X. U.S. Patent 6,274,752 Bl, 2001.
18. (d) Marks. T. J.; Chen. Y.-X. U.S. Patent 6,403,732 B2, 2002.
19. (e) Marks. T. J.; Chen. Y.-X. U.S. Patent 6, 388, 114 B1, 2002.
20. Campbell. R. E., Jr. (The Dow Chemical Co.) U.S. Patent 4,665,046. 1987.
21. (a) Marks, T. J. Acc. Chem. Res. 1992, 25, 57.
22. (b) Finch, W. C; Gillespie. R. D.; Hedden, D.; Marks, T. J. J. Am. Chem. Soc. 1990. 112. 6221.
23. (c) Hedden, D.; Marks, T. J. J. Am. Chem. Soc. 1988, 110, 1647.
24. (d) Toscano, P. J.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 653.
25. (e) He, M.-Y.; Xiong, G.; Toscano, P. J.; Burwell, R. L., Jr.; Marks, T. J.J. Am. Chem. Soc. 1985, 107, 641.
26. 4] are accessible as part of an equilibrium that lies well to the side of the starting materials: ref 4.
27. Evans, W. J.; Kozimor, S. A.; Ziller, J. W. Organometallics 2005, 24, 3407.
28. 3: ref 15.
29. Monreal, M. J.; Diaconescu, P. L. Organometallics 2008, 27, 1702.
30. 4] has also been reported: (a) Cendrowski-Guillaume, S. M.; Lance, M.; Nierlich, M.; Ephritikhine, M. Organometallics 2000. 19. 3257.
31. Moisan, L.; Le Borgne, T.; Villiers, C.; Thuery, P.; Ephritikhine, M. C. R. Chimie 2007, 10, 883.
32. 4] have been reported: (a) ref 6b.
33. Dash, A. K.; Wang, J. X.; Berthet, J.-C; Ephritikhine, M.; Eisen, M. S. J. Organomet. Chem. 2000, 604, 83.
34. (a) Piers, W. E.; Emslie, D. J. H. Coord. Chem. Rev. 2002, 233, 131.
35. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102. 1851.
36. (c) Marques, N.; Sella, A.; Takats, J. Chem. Rev. 2002, 102, 2137.
37. (a) Shannon, R. D. Acta Crystallogr. 1976, A32, 751.
38. (b) Cordero, B.; Gómez, V.; Platero-Prats, A. E.; Revés, M.; Echeverría, J.; Cremades, E.; Barragán, F.; Alvarez, S. Dalton Trans. 2008, 2832.
39. (a) Marks, T. J.; Day, V. W. Actinide Hydrocarbyl and Hydride Chemistry. In Fundamental and Technological Aspects of Organo-f-Element Chemistry, Nato Science Series C; Marks, T. J., Fragalá, I. L., Eds.; D. Reidel Publishing Co.: Dordrecht, The Netherlands, 1985; Vol. 155, p 115.
40. Castro-Rodríguez, I.; Meyer. K. Chem. Commun. 2006, 1353.
41. (c) Ephritikhine, M. Dalton Trans. 2006, 2501.
42. (d) Barnea. E.; Eisen, M. S. Coord. Chem. Rev. 2006, 250, 855.
43. (e) Burns, C. J.; Eisen, M. S. Organoactinide Chemistry: Synthesis and Characterization. In The Chemistry of the Transactinide Elements, 3rd ed.; Morss, L. R., Edelstein, N. M., Fuger, J., Eds.; Springer: Dordrecht, The Netherlands, 2006; Vol. 5, p 2799.
44. (f) Burns, C. J.; Eisen, M. S. Homogeneous and Heterogeneous Catalytic Processes Promoted by Organoactinides. In The Chemistry of the Transactinide Elements, 3rd ed.; Morss, L. R., Edelstein, N. M., Fuger, J., Eds.; Springer: Dordrecht, The Netherlands, 2006; Vol. 5, p 2911.
45. Kaltsoyannis, N.; Hay, P. J.; Li, J.; Blaudeau, J.-P.; Bursten, B. E. Theoretical Studies of the Electronic Structure of Compounds of the Actinide Elements. In The Chemistry of the Transactinide Elements, 3rd ed.; Morss, L. R., Edelstein, N. M., Fuger. J., Eds.; Springer: Dordrecht, The Netherlands, 2006; Vol. 3, p 1893.
46. 2] (X = OR or halide) may be closer to cerium(IV) than to cerium(III):(a) Noh, W.; Girolami, G. S. Polyhedron 2007, 26, 3865.
47. Casely, I. J.; Liddle, S. T.; Blake, A. J.; Wilson, C; Arnold, P. L. Chem. Commun. 2007, 5037.
48. Evans, W. J.; Deming, T. J.; Ziller, J. W. Organometallics 1989, 8, 1581.
49. (d) Edelstein, N. M.; Allen, P. G.; Bucher. J. J.; Shuh, D. K.; Sofield, C. D.; Kaltsoyannis, N.; Maunder, G. H.; Russo, M. R.; Sella, A. J. Am. Chem. Soc. 1996, 118, 13115.
50. (e) Ashley, A.; Balazs, G.; Cowley, A.; Green, J.; Booth, C. H.; O'Hare, D. Chem. Commun. 2007. 1515.
51. Substrate specificity, co-polymerization opportunities, degree of branching, polymerization by high activity single component catalysts, etc.
52. Guérin, F.; McConville, D. H.; Vittal, J. J. Organometallics 1996, 15, 5586.
53. Cruz, C. A.; Emslie, D. J. H.; Harrington, L. E.; Britten, J. E.; Robertson, C. M. Organometallics 2007, 26. 692.
54. For the synthesis of N-mesityl- and N-cyclohexyl-substituted 4,5-bis(amido)xanthene ligands, and the preparation of titanium(IV) bis(amido) and dibenzyl complexes, see: Porter, R. M.; Danopoulos, A. A. Polyhedron 2006, 25, 859.
55. Cruz, C. A.; Emslie, D. J. H.; Harrington, L. E.; Britten, J. F. Organometallics 2008, 27, 15.
56. Bruno, J. W.; Smith, G. M.; Marks, T. J.; Fair, C. K.; Schultz, A. J.; Williams, J. M. J. Am. Chem. Soc. 1986, 108, 40.
57. Coates. G. W. Chem. Rev. 2000, 100, 1223.
58. Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391.
59. (a) Scollard, J. D.; McConville. D. H.; Payne, N. C.; Vittal, J. J. Macromolecules 1996. 29, 5241.
60. (b) Scollard. J. D.; McConville. D. H. J. Am. Chem. Soc. 1996, 118. 10008.
61. (a) Hayes, P. G.; Piers, W. E.; Parvez, M. J. Am. Chem. Soc. 2003, 125. 5622.
62. (b) Hayes. P. G.; Piers. W. E.; Parvez. M. Chem.-Eur. J. 2007. 13, 2632.
63. Lancaster, S. J.; Robinson, O. B.; Bochmann, M.; Coles, S. J.; Hursthouse. M. B. Organometallics 1995, 14. 2456.
64. (a) Gillis. D. J.; Tudoret, M.-J.; Baird. M. C. J. Am. Chem. Soc. 1993, 115, 2543.
65. (b) Wang, Q.; Quyoum, R.; Gillis, D. J.; Tudoret, M.-J.; Jeremic, D.; Hunter, B. K.; Baird, M. C. Organometallics 1996, 15, 693.
66. (c) Gillis, D. J.; Quvoum, R.; Tudoret, M.-J.; Wang, Q.; Jeremic, D.; Roszak, A. W.; Baird, M. C. Organometallics 1996, 15, 3600.
67. (37) Chen, Y.-X.; Marks, T. J. Organometallics 1997, 16, 3649.
68. 1H NMR spectrum was not obtained.
69. (a) Horton, A. D.; de With, J. Organometallics 1997, 16, 5424.
70. Pellecchia, C; Immirzi. A.; Grassi, A.; Zambelli, A. Organometallics 1993, 12, 4473.
71. 5Br.
72. 4] in benzene or toluene also resulted in precipitation of an insoluble orange-brown oil. However, in this case, the product was insufficiently soluble in benzene or toluene to allow investigation by solution NMR spectroscopy, and crystals of the product could not be obtained.
73. Crystals of 5, 6, and 7 were always coated with a viscous oil, which prevented investigation by elemental analysis.
74. C,H coupling constant.
75. 8-THF used.
76. 1H NMR spectrum.
77. 4] coated the walls of the reaction vessel. This prevented direct NMR spectroscopy of the oils using an NMR insert.
78. (a) van der Waals radii: U = 1.86 Å, C = 1.70 Å. Bondi, A. J. Phys. Chem. 1964, 68, 441. The van der Waals radius of Th can be predicted to be approximately 1.91 Å
79. (b) Atomic radii in crystals: Th = 1.80 Å, U = 1.75 Å, C = 0.70 Å. Slater, J. C. J. Chem. Phys. 1964, 41, 3199.
80. 4+ 0.89 Å. Shannon, R. D. Acta Crystallogr. 1976, A32, 751.
81. The two sets of Th - N and Th - O bond distances listed for compound 3 correspond to two distinct molecules in the unit cell.
82. (a) Campbell, G. C.; Cotton, F. A.; Haw, J. F.; Schwotzer, W. Organometallics 1986, 5, 274.
83. (b) Cotton. F. A.; Schwotzer. W. Organometallics 1985, 4, 942.
84. (50) Cotton, F. A.; Schwotzer, W.; Simpson, C. Q. Angew. Chem., Int. Ed Engl. 1986, 25, 637.
85. (51) (a) Cotton, F. A.; Schwotzer, W. Organometallics 1987, 6, 1275.
86. (b) Cesari, M.; Pedretti, U.; Zazzetta, A.; Lugli, G.; Marconi. W. Inorg. Chim. Acta 1971, 5. 439.
87. (c) Garbar, A. V.; Leonov, M. R.; Zakharov, L. N.; Struchkov, Y. T. Russ. Chem. Bull. 1996, 45, 451.
88. (a) Fan, B.; Shen, Q.; Lin, Y. J. Organomet. Chem. 1989, 376. 61.
89. Fan. B.; Shen, Q.; Lin. Y. J. Organomet. Chem. 1989. 377. 51.
90. (c) Cotton, F. A.; Schwotzer, W. J. Am. Chem. Soc. 1986, 108, 4657.
91. Manriquez, J. M.; Fagan, P. J.; Marks, T. J. J. Am. Chem. Soc. 1978, 100, 3939.
92. The strong tendency to engage in π-arene bonding in this chemistry may also be related to increased covalency in metal - ligand bonding, relative to the trivalent lanthanide metals, and the potential for f-orbital involvement in bonding.
93. 3, the products resisted crystallization.
94. 4]: (a) ref 6b;
95. (b) ref 13a.
96. Note that in complex 9, the positions (axial or in-plane) of the coordinated benzylborate and alkyl ligand are not known.
97. Burger, B. J.; Bercaw, J. E. Vacuum Line Techniques for Handling Air-Sensitive Organometallic Compounds. Experimental Organometallic Chemistry - A Practicum in Synthesis and Characterization; American Chemical Society: Washington, DC, 1987; Vol. 357. p 79.
98. Bailey, P. L.; Coxall, R. A.; Dick, C. M.; Fabre, S.; Henderson, L. C; Herber. C; Liddle. S. T.; Lorono-Gonzalez, D.: Parkin, A.; Parsons, S. Chem.-Eur. J. 2003. 9. 4820.
99. Sluis, P. V. D.; Spek, A. L. Acta Crystallogr. 1990, A46, 194.